MX9702768A - Novel effective and high enantiomeric selectivity process for the production of enantiomerically pure cyclopentane-beta-aminoacids. - Google Patents

Novel effective and high enantiomeric selectivity process for the production of enantiomerically pure cyclopentane-beta-aminoacids.

Info

Publication number
MX9702768A
MX9702768A MX9702768A MX9702768A MX9702768A MX 9702768 A MX9702768 A MX 9702768A MX 9702768 A MX9702768 A MX 9702768A MX 9702768 A MX9702768 A MX 9702768A MX 9702768 A MX9702768 A MX 9702768A
Authority
MX
Mexico
Prior art keywords
enantiomerically pure
aminoacids
beta
production
cyclopentane
Prior art date
Application number
MX9702768A
Other languages
Spanish (es)
Other versions
MXPA97002768A (en
Inventor
Joachim Mittendorf
Original Assignee
Bayer Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Ag filed Critical Bayer Ag
Publication of MX9702768A publication Critical patent/MX9702768A/en
Publication of MXPA97002768A publication Critical patent/MXPA97002768A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/30—Preparation of optical isomers
    • C07C227/32—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The present invention discloses a novel, efficient and high enantiomeric selectivity process for the production of enantiomerically pure cyclopentane- beta-aminoacids. The process according to the invention for the production of enantiomerically pure cyclopentane- beta-aminoacids of general formula (I), wherein A and D are as described in the specification, is characterized in that mesodicarboxylic anhydrides are transformed through asymmetric alcoholysis using allylic alcohols in the presence of an enantiomerically pure chiral aminated base, in inert solvents first through an enantiomerically pure saline intermediate step, in enantiomerically pure dicarboxylic acid monoester, in a further step said dicarboxylic acid monoester is transformed in the direction of a Curtius transportation by reacting it with azides into corresponding intermediate acid azides, and subsequently into corresponding transposed isocyanates, said isocyanates being subsequently transformed into compounds of general formula (VII) using allylic alcohols, and cyclopentane- beta-aminoacids of general formula (II) are produced by dissociation of urethane and ester functions.
MXPA/A/1997/002768A 1996-05-03 1997-04-16 New effective and high selectivity procedureanantiomerica for the production of ciclopentano-beta- aminoacidos enantiomericamente pu MXPA97002768A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19617772A DE19617772A1 (en) 1996-05-03 1996-05-03 New efficient and highly enantioselective process for the production of enantiomerically pure cyclopentane-beta-amino acids
DE19617772.3 1996-05-03

Publications (2)

Publication Number Publication Date
MX9702768A true MX9702768A (en) 1997-11-29
MXPA97002768A MXPA97002768A (en) 1998-07-03

Family

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Also Published As

Publication number Publication date
NO971983L (en) 1997-11-04
HRP970214A2 (en) 1998-04-30
ZA973796B (en) 1997-12-01
EP0805145B1 (en) 2001-10-31
ID16859A (en) 1997-11-20
US5877343A (en) 1999-03-02
JPH1087586A (en) 1998-04-07
KR970074749A (en) 1997-12-10
DK0805145T3 (en) 2002-03-04
AR006944A1 (en) 1999-09-29
PL319775A1 (en) 1997-11-10
DE19617772A1 (en) 1997-11-13
CZ135397A3 (en) 1998-05-13
AU1915697A (en) 1997-11-06
AR013071A2 (en) 2000-12-13
EP0805145A1 (en) 1997-11-05
IL120747A0 (en) 1997-09-30
ATE207876T1 (en) 2001-11-15
SI0805145T1 (en) 2002-02-28
ES2166930T3 (en) 2002-05-01
PT805145E (en) 2002-03-28
CN1168883A (en) 1997-12-31
CA2204055A1 (en) 1997-11-03
HU9700831D0 (en) 1997-06-30
DE59705135D1 (en) 2001-12-06
SK55497A3 (en) 1997-11-05
SV1997000031A (en) 1997-10-23
BR9701983A (en) 1998-09-15
NO971983D0 (en) 1997-04-29

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